Diethyl Ether → 2-(4-Methylpiperazin-1-yl)propan-1-amine

HRID 614478Notes

Reaction equation

HRID 614478 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH:8]([CH3:11])[C:9]#[N:10])[CH2:4][CH2:3]1.CCOCC.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH:8]([CH3:11])[CH2:9][NH2:10])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 213278122-(4-Methylpiperazin-1-yl)propanenitrile

Product 1

HCID 166414572-(4-Methylpiperazin-1-yl)propan-1-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2-(4-Methyl-1-piperazinyl)propionitrile (38.3 g.) in 50 ml. of dry ether is added in a dropwise manner to a stirred solution of 19 g. of lithium aluminum hydride in 600 ml. of dry ether. The resulting mixture is heated at reflux for 1 hour, cooled and treated in sequence with 10 ml. of water, 7.5 ml. of 20% aqueous sodium hydroxide, and 35 ml. of water. The mixture is filtered and the filtrate is evaporated. The residue is fractionated at reduced pressure to give 2-(4-methyl-1-piperazinyl)propylamine as an oil, b.p. 92°-93° C./9 mm.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for 1 hour
  3. temperaturecooled
  4. additiontreated in sequence with 10 ml
  5. filtrationThe mixture is filtered
  6. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-47b7972d5e5f4b538e9a934096b9b34b
Source dataset
uspto-grants-1979_03
Patent number
US04145347

Reaction notes

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